Jefferson Street Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Jefferson Street
Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Lexington
Downtown Lexington
CA $882
per person
Sep 11 - Sep 13
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Lexington (LEX)
8.8/10 Excellent! (1,004 reviews)
We had a wonderful stay at the Hyatt. Shout out especially to Peter at the Registration desk who was so personable and helpful. Even though Barry Manilow had to cancel his concert, Peter sang Copacabana for us!
All of the staff and accommodations were amazing! I can very highly recommend Hyatt Regency Lexington.
Reviewed on Aug 5, 2026
21c Museum Hotel Lexington
Downtown Lexington
CA $1,011
per person
Sep 11 - Sep 13
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)
Coffee maker would not work in the room, toilet was not functioning when I arrived, restaurant and bar were under construction, a few signs of wear and tear in the units.
Reviewed on Aug 7, 2026
Elwood Hotel & Suites
CA $2,588
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Lexington (LEX)
9.4/10 Exceptional! (1,129 reviews)
Great charming place! Staff were excellent- Trace the bartender was a true artist with cocktails! Rooms were clean, super quiet and had a lot of space! Will recommend to anyone coming to town!
Reviewed on Aug 7, 2026
Where to stay in Jefferson Street
Find the best Jefferson Street areas and neighborhoods for the activities you enjoy most. Learn more about Jefferson Street
Downtown Lexington
1 out of top 10 points of interest in this area
While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.
Northside District
If you're spending some time in Northside District, Lexington Opera House and West Sixth Brewing are top sights worth seeing.
Liberty Area
1 out of top 10 points of interest in this area
If you're spending some time in Liberty Area, Hamburg Place and Hamburg Pavilion are top sights worth seeing.
Historic South Hill
While Historic South Hill might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lexington Memorial Coliseum and Rupp Arena.
Georgetown
If you're looking for some top things to see and do in Georgetown and surrounding area, you can visit Rupp Arena and Lexington Opera House.
Jefferson Street Hotel Deals
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
CA $162
CA $216 total
Sep 7 - Sep 8
includes taxes & fees
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
CA $225
CA $285 total
Sep 7 - Sep 8
includes taxes & fees
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
CA $159
CA $184 total
Aug 16 - Aug 17
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Things to do
Unique Horse Farm Tours with Insider Access to Private Farms
CA $83
per adult
90% of travellers recommend
Lexington: Downtown Walking Food & History Tour
CA $139
per adult
100% of travellers recommend
Bites of the Bluegrass Cocktails & Bites Tour
CA $176
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.